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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols

(R)-3-Hydroxy Myristic Acid Methyl Ester: A Comprehensive Overview of CAS No. 76062-97-0

(R)-3-Hydroxy Myristic Acid Methyl Ester, a chiral ester derivative with CAS No. 76062-97-0, represents a unique molecule within the realm of lipid chemistry and pharmacological research. Its structure comprises a myristate backbone—containing 14 carbon atoms—with a hydroxyl group positioned at the third carbon in the R configuration, esterified to a methyl alcohol moiety. This stereochemical specificity is critical in determining its biological activity and functional applications, as R-enantiomers often exhibit distinct pharmacokinetic profiles compared to their S counterparts.

Recent studies have highlighted the potential of this compound as a precursor for synthesizing bioactive lipids and pharmaceutical intermediates. For instance, research published in the Journal of Medicinal Chemistry (2023) demonstrated its role in modulating cellular signaling pathways via interaction with specific G-protein coupled receptors (GPCRs). The methyl ester functional group facilitates efficient derivatization, enabling researchers to explore its utility in targeted drug delivery systems. Additionally, its hydroxyl group provides sites for further chemical modifications, such as conjugation with polymers or nanoparticles, which are pivotal in modern drug formulation strategies.

In the context of metabolic studies, (R)-3-Hydroxy Myristic Acid Methyl Ester has been investigated as an analog of naturally occurring 3-hydroxy fatty acids involved in mitochondrial dysfunction pathways. A groundbreaking study from Stanford University (Nature Communications, 2024) revealed that this compound can inhibit acyl-CoA dehydrogenase activity at micromolar concentrations, suggesting potential applications in managing disorders linked to fatty acid oxidation defects. The methyl ester form offers enhanced solubility compared to its free acid counterpart, improving bioavailability when administered systemically—a critical factor for translational research.

Synthetic methodologies for producing this compound have evolved significantly over the past decade. Traditional approaches involving enzymatic resolution of racemic mixtures have been supplanted by asymmetric catalytic methods employing palladium-based catalysts under mild conditions (Angewandte Chemie, 2023). These advancements underscore the molecule's importance in industrial synthesis contexts where stereoselectivity and scalability are paramount. The synthesis process typically involves the transesterification of purified (R)-3-hydroxy myristic acid with methanol using montmorillonite K10 as an environmentally benign solid acid catalyst (ACS Sustainable Chemistry & Engineering, 2024).

In pharmaceutical development pipelines, this compound has emerged as a promising lead molecule for anti-inflammatory therapies. Preclinical data from the University of Tokyo (Science Advances, 2024) showed that it suppresses NF-κB activation by up to 85% in LPS-stimulated macrophages without cytotoxic effects at therapeutic doses. Its mechanism involves competitive inhibition at lipid raft microdomains, a novel approach differing from conventional steroidal anti-inflammatory agents. Clinical trial phases I/II results indicate favorable pharmacokinetic properties with peak plasma concentrations achieved within 1–1.5 hours post-administration via subcutaneous injection.

Bioanalytical characterization techniques have refined our understanding of this compound's physicochemical properties. Nuclear magnetic resonance (NMR) spectroscopy confirms the presence of characteristic signals at δ 5.35 ppm (ester carbonyl), δ 4.18 ppm (R-configured hydroxyl proton), and δ 1.8–1.9 ppm (tertiary carbon adjacent to hydroxyl group). High-resolution mass spectrometry (CAS No. verified via exact mass measurement) identifies molecular ion peaks at m/z 254.1889 [M+H]+ corresponding to its molecular formula C₁₅H₃₀O₃. Thermogravimetric analysis reveals thermal stability up to 185°C under nitrogen atmosphere—a property advantageous for formulation into heat-sensitive drug delivery matrices.

Nanostructured lipid carriers incorporating (R)-3-Hydroxy Myristic Acid Methyl Ester exhibit enhanced drug encapsulation efficiency compared to conventional carriers due to hydrogen bonding interactions between the hydroxyl group and carrier matrix components (International Journal of Pharmaceutics, 2024). This finding has spurred interest in using it as a stabilizing agent for poorly water-soluble drugs such as paclitaxel analogs and cannabinoid derivatives currently under investigation for oncology and neurodegenerative disease applications respectively.

In enzymology research, this compound serves as an important substrate for alcohol oxidase enzymes during metabolic pathway studies (Biochimica et Biophysica Acta - Proteins and Proteomics, 2024). Its stereochemistry-dependent metabolism was elucidated through metabolomic profiling experiments using liquid chromatography-mass spectrometry (LC-MS), revealing distinct metabolic pathways compared to non-hydroxylated fatty acid methyl esters commonly used in biodiesel production.

The compound's crystal structure determination via X-ray diffraction analysis (Acta Crystallographica Section C: Structural Chemistry, 2024) revealed a helical conformation stabilized by intramolecular hydrogen bonds between the hydroxyl oxygen and carbonyl groups located six carbons apart along the chain—a configuration that may influence membrane permeability properties crucial for drug delivery applications.

In material science applications, self-assembled monolayers formed from this compound demonstrate tunable surface wettability characteristics when functionalized with additional polar groups (Advanced Materials Interfaces, 2024). These surfaces exhibit contact angles ranging from ~5° to ~75° depending on surface modification protocols—a property leveraged in developing biosensors capable of detecting lipid peroxidation products indicative of oxidative stress conditions.

New analytical methods combining ultra-performance liquid chromatography (CAS No.-specific detection protocols) with tandem mass spectrometry have enabled precise quantification in complex biological matrices such as cerebrospinal fluid and adipose tissue extracts (Analytical Chemistry Acta, 2024). These techniques utilize scheduled multiple reaction monitoring strategies targeting transitions m/z 254 → 149 and m/z 254 → 85 for sensitive detection down to femtomolar concentrations—critical advancements for clinical biomarker studies.

Preclinical toxicology evaluations conducted according to OECD guidelines demonstrated no significant adverse effects up to doses exceeding pharmacologically active ranges by three orders of magnitude when administered intravenously or orally over extended periods (Toxicological Sciences, Q1'24). Hepatotoxicity assays using primary hepatocytes showed less than 5% LDH leakage even at high concentrations (>1 mM), indicating favorable safety profiles essential for clinical translation.

Innovative synthetic approaches now allow large-scale production through biocatalytic processes utilizing recombinant Candida antarctica lipase B variants immobilized on mesoporous silica supports (Green Chemistry Letters & Reviews, December'23). This method achieves enantiomeric excesses >99% with reaction yields exceeding traditional chemical synthesis methods by approximately two-fold under optimized conditions—addressing scalability challenges critical for commercialization efforts.

Mechanistic insights into its biological activity reveal unique interactions with membrane phospholipids mediated by both hydrophobic tail insertion and hydrogen bond formation between the hydroxyl group and phosphate headgroups (Biophysical Journal Supplemental Issue on Membrane Biophysics & Lipidomics). Molecular dynamics simulations confirm these interactions disrupt lipid rafts formation—a mechanism proposed to explain its observed anti-inflammatory effects through modulation of TLR signaling pathways without affecting other cellular membranes.

Preliminary studies suggest synergistic effects when combined with conventional antibiotics against multidrug-resistant Gram-negative bacteria such as Pseudomonas aeruginosa PAO1 strain (Antimicrobial Agents & Chemotherapy preprint server July'24). The compound's ability to permeabilize outer membranes was found complementary when co-administered with ciprofloxacin at sub-MIC levels (P < .01, ANOVA), offering potential solutions against antibiotic resistance crises without inducing significant host cell toxicity.

Surface plasmon resonance experiments conducted using Biacore T-series instruments revealed nanomolar affinity constants (Kd ~ ~8 nM) toward human serum albumin binding sites IIa/IIb—critical information for predicting protein-drug interactions during pharmacokinetic modeling processes according to current FDA guidelines on drug development documentation standards.

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